title: Liquid chromatographic resolution of racemic rasagiline and its analogues on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid.
abstract: A liquid chromatographic chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was applied to the resolution of 15 analytes, including racemic rasagiline, a chiral drug for the treatment of Parkinson's disease, and its analogues. The composition of mobile phase was optimized to be ethanol/acetonitrile/acetic acid/triethylamine (80:20:0.2:0.3, v/v/v/v) by evaluating the chromatographic results for the resolution of five selected analytes under various mobile phase conditions. Under the optimized mobile phase conditions, racemic rasagiline was resolved quite well with a separation factor of 1.48 and resolution of 2.71 and its 14 analogues were also resolved reasonably well with separation factors of 1.06-1.54 and resolutions of 0.54-2.11. Among 15 analytes, racemic rasagiline was resolved best except for just one analyte. The analyte structure-enantioselectivity relationship indicated that racemic rasagiline has the most appropriate structural characteristics for resolution on the chiral stationary phase.
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan, Republic of Korea.
authors.forename: Kyung Mi
authors.initials: KM
authors.lastname: Tak
authors.forename: Eun Ju
authors.initials: EJ
authors.lastname: Park
authors.forename: Myung Ho
authors.initials: MH
authors.lastname: Hyun
mesh_terms: D000978:Antiparkinson Agents / Q000737:chemistry; D002853:Chromatography, Liquid; D043844:Crown Ethers / Q000737:chemistry*; D007189:Indans / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000978:Antiparkinson Agents; D043844:Crown Ethers; D007189:Indans; C031967:rasagiline; C090732:18-crown-6 2,3,11,12-tetracarboxylic acid
keywords: 18-Crown-6; Chiral stationary phases; Enantiomeric separation; LC; Rasagiline